Chen Daixiang, Bao Yu, Yan Shenghu, Wang Jiayin, Zhang Yue, Li Guigen
School of Pharmacy, Changzhou University, Changzhou 213164, China.
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409, USA.
Molecules. 2024 Feb 8;29(4):782. doi: 10.3390/molecules29040782.
We present the first example of visible-light-mediated multicomponent annulation of 1,7-diynes by taking advantage of quadruple cleavage olf carbon-halogen bonds of BrCCl to generate a C1 synthon, which was adeptly applied to the preparation of skeletally diverse 3-benzoyl-quinolin-2(1)-one acetates in moderate to good yields. Controlled experiments demonstrated that HO acted as both oxygen and hydrogen sources, and -dichlorovinyl carbonyl compound exhibited as a critical intermediate in this process. The mechanistic pathway involves Kharasch-type addition/6-exo-dig cyclization/1,5-(SN")-substitution/elimination/binucleophilic 1,6-addition/proton transfer/tautomerization sequence.
我们通过利用BrCCl中碳-卤键的四重裂解生成C1合成子，展示了可见光介导的1,7-二炔多组分环化反应的首个实例，该反应被巧妙地应用于以中等至良好产率制备骨架多样的3-苯甲酰基喹啉-2(1)-酮乙酸酯。对照实验表明，HO既作为氧源又作为氢源，并且二氯乙烯基羰基化合物在此过程中表现为关键中间体。其反应机理途径涉及卡拉施型加成/6-外向-双环化/1,5-(SN")-取代/消除/双亲核1,6-加成/质子转移/互变异构序列。
